Alkaloids from leaves and bark ofAlstonia scholaris in the Philippines

Yamauchi, Tatsuo; Abe, Fumiko; Padolina, William G.; Dayrit, Fabian M

doi:10.1016/0031-9422(90)80208-x

Cited by 62 publications

(36 citation statements)

References 15 publications

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“…New alkaloid 5 is an N(4)-oxide derivative of 4. Other known alkaloids are tubotaiwine (6) [11], 19(R)-methoxytubotaiwine [12], 19(S)-methoxytubotaiwine [12], (E)-condylocarpine [13], and (E)-condylocarpine N-oxide [14]. In this paper, we describe the isolation and structure elucidation of new compounds 1-5 ( Fig.…”

Section: Introductionmentioning

confidence: 97%

“…The proximity of this fragment to C-2 and C-8 was suggested by the observed HMBC correlations of H-6 with C-2 and C-8. kopsiyunnanine F2 (2) isocondylocarpine N-oxide (5) [11]. The chemical shift d C 63.7 suggested that C-20 was associated with an oxygen atom, and the HMBC correlation of H 3 -18 with C-20 suggested the direct correlation of C-20 with the oxygenated -CH-CH 3 group.…”

Section: Introductionmentioning

confidence: 97%

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Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan Kopsia arborea

Kitajima

Kogure

et al. 2009

J Nat Med

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Five new alkaloids, including three 19,20-epoxytubotaiwine stereoisomers, viz. kopsiyunnanines F1 (1), F2 (2), and F3 (3), (Z)-isocondylocarpine (4), and (Z)-isocondylocarpine N-oxide (5), along with five known tubotaiwine-type indole alkaloids were isolated from the aerial part of Yunnan Kopsia arborea Blume (Apocynaceae). Their structures including absolute configurations were elucidated by spectroscopic and chemical means.

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Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 97%

Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan Kopsia arborea

Kitajima

Kogure

et al. 2009

J Nat Med

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“…The assigned structures (1, 2, and 3) were in complete agreement with the reported values. [3,15,16] The reference markers 1, 2, and 3 were isolated in high purity (Ca. > 95%), determined by HPLC-PDA analysis in our laboratory.…”

Section: Reference Compounds and Chemicalsmentioning

confidence: 99%

Silica-Based Monolithic Coupled Column for the Simultaneous Determination of Echitamine, N^b-Demethylalstogustine, and Loganetin in Alstonia scholaris by RP-HPLC and Optimization of Extraction Method

Maurya

Verma

Srivastava

2015

Journal of Liquid Chromatography & Related Technologies

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A simple, rapid, and sensitive high performance liquid chromatography (HPLC) method for the simultaneous quantification of echitamine (1), N b -demethylalstogustine (2), and loganetin (3) in Alstonia scholaris was developed using silica-based monolithic coupled column. The samples were analyzed on Chromolith RP-18 coupled column (100 þ 50 ¼ 150 mm Â 4.6 mm) using isocratic elution with acetonitrile: 0.01 M buffer (KH 2 PO 4 ) containing 0.1% trifluoroacetic acid (20:80, v=v) at 0.5 mL=min flow rate and detection at 254 nm. The limits of detection and quantitation were 0.64 and 2.15 mg=mL for echitamine, 0.72 and 2.43 mg=mL for N b -demethylalstogustine, and 0.78 and 2.62 mg=mL for loganetin, respectively. Standard curves were linear in the range of 3-15 mg=mL (r 2 ¼ 0.999). The method showed good repeatability (%RSD < 1.14), reproducibility (%RSD < 1.16), and recovery (mean% > 99.48). This is the first report on loganetin isolation from A. scholaris. Furthermore, various extraction methods and parameters were investigated to optimize markers extraction from the sample matrix. Finally, the optimized extraction method was used in the extraction of markers from different parts of the plant. The validated method was successfully used in the quantification of markers in various parts of the plant, which can be applied in the overall quality assessment of A. scholaris.

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“…The leaves and bark of Alstonia sholaris have also been reported to contain alkaloids like Lagumamine (19-hydroxytubotaiwine), angustilobine B acid, losbanine (6,7-seco-6-norangustilobine B), tubotaiwine, its oxide, 6,7-secoangustilobine B, 17-0-Acetyl echitamine and echitamine 16 . It has also been reported to possess other alkaloids including 19-epischolaricine, Nbmethylscholarcine, Na-methylburnamine and vallesamine Nb-oxide, picrinine, nareline, and alschomine 14 .…”

Section: Identification Of the Compoundmentioning

confidence: 99%

“…Similarly, it has been found to contain other alkaloids like 19-epischolaricine, Nbmethylscholarcine, Na-methylburnamine and vallesamine Nb-oxide, picrinine, nareline, alschomine, and angustilobine 16 . The Alstonia glaucescens have been reported to consist indole alkaloids such as 17-O-acetyl-Nb-demethyl echitamine, echitamidine-N-Oxide, echitaminic acid, sweroside, echitamidine, Nb-demethyl echitamine, 20-epi-19-echitamidine, N-bdemethylechtamine-N-oxide and echitamine 17 .…”

Section: Introductionmentioning

confidence: 99%

Untitled

2016

IJPSR

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ABSTRACT:The non-infected bark of Alstonia scholaris R. Br. was carefully peeled off, shade dried, and coarsely powdered with the help of a hand club. Powdered dried bark was extracted in 95% ethanol at room temperature and evaporated in vacuo (40°C). The ethanolic extract was suspended in distilled water and subsequently extracted in hexane, chloroform, ethyl acetate and n-butanol. The solvent of each fraction was removed in a rotary vacuum evaporator under reduced pressure. The crude chloroform extract was mixed with 3% HCl and ethanol. The aqueous layer was collected and the pH was adjusted to 10 by adding NaOH, thereafter it was further extracted with chloroform to get a crude alkaloidal fraction. The alkaloidal fraction was subjected to column chromatography over silica gel and eluted with chloroform: methanol (50:50). The elutes between fractions 40-100 were collected and subjected to preparative HPTLC in the solvent system of ethyl acetate: benzene (1:1). The HPTLC showed the presence of two alkaloids, which were evaluated for their cytotoxic effects in neoplastic cell lines by MTT assay. The compound which showed greater cytotoxicity was subjected to UV, NMR, Mass, and IR spectra and identified as echitamidine-N-oxide-19--β-D-glucopyranoside (EOG). The presence of EOG in the chloroform fraction was further confirmed by semipreparative RPHPLC (H 2 O/CH 3 CN-0%-80%; CH 3 CN in 80 min, flow rate 3 mL/min, UV detector - 250 nm) and was also identified based on the literature.

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Alkaloids from leaves and bark ofAlstonia scholaris in the Philippines

Cited by 62 publications

References 15 publications

Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan Kopsia arborea

Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan Kopsia arborea

Silica-Based Monolithic Coupled Column for the Simultaneous Determination of Echitamine, N^b-Demethylalstogustine, and Loganetin in Alstonia scholaris by RP-HPLC and Optimization of Extraction Method

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Alkaloids from leaves and bark ofAlstonia scholaris in the Philippines

Cited by 62 publications

References 15 publications

Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan Kopsia arborea

Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan Kopsia arborea

Silica-Based Monolithic Coupled Column for the Simultaneous Determination of Echitamine, Nb-Demethylalstogustine, and Loganetin in Alstonia scholaris by RP-HPLC and Optimization of Extraction Method

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Silica-Based Monolithic Coupled Column for the Simultaneous Determination of Echitamine, N^b-Demethylalstogustine, and Loganetin in Alstonia scholaris by RP-HPLC and Optimization of Extraction Method